HRP20201767T1 - Proton-binding polymers for oral administration - Google Patents

Proton-binding polymers for oral administration Download PDF

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HRP20201767T1
HRP20201767T1 HRP20201767TT HRP20201767T HRP20201767T1 HR P20201767 T1 HRP20201767 T1 HR P20201767T1 HR P20201767T T HRP20201767T T HR P20201767TT HR P20201767 T HRP20201767 T HR P20201767T HR P20201767 T1 HRP20201767 T1 HR P20201767T1
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cross
pharmaceutical composition
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amine
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Gerrit Klaerner
Eric F. Connor
Randi K. Gbur
Matthew J. Kade
Paul H. Kierstead
Jerry M. Buysse
Michael J. Cope
Kalpesh N. Biyani
Son H. Nguyen
Scott M. Tabakman
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Tricida Inc.
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    • A—HUMAN NECESSITIES
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    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/74—Synthetic polymeric materials
    • A61K31/785—Polymers containing nitrogen
    • A—HUMAN NECESSITIES
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • C08F226/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a single or double bond to nitrogen
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    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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Claims (18)

1. Farmaceutski sastav za upotrebu u liječenju metaboličke acidoze, gdje farmaceutski sastav sadrži umreženi aminski polimer koji veže protone koji sadrži ostatak amina koji odgovara Formuli 2b i umreženi aminski polimer je dobiven radikalskom polimerizacijom amina koji odgovara formuli 2b: [image] gdje m i n su nezavisno ne-negativni cijeli brojevi; svaki R12 je nezavisni vodik, supstituirani hidrokarbil ili hidrokarbil; R22 i R32 su nezavisni vodik, supstituirani hidrokarbil ili hidrokarbil; R42 je vodik, hidrokarbil ili supstituirani hidrokarbil; X1 je [image] X2 je alkil, aminoalkil ili alkanol; svaki X13 je nezavisni vodik, hidroksi, alicikličan, amino, aminoalkil, halogen, alkil, heteroaril, boronska kiselina ili aril; z je broj koji nije negativan; i amin koji odgovara Formuli 2b sadrži najmanje jednu alil grupu i umreženi aminski polimer ima (i) ravnotežni kapacitet vezivanja protona od najmanje 5 mmol/g i kapacitet vezivanja kloridnih iona od najmanje 5 mmol/g, u vodenom puferu simulirane želučane tekućine ("SGF") koji sadrži 35 mM NaCl i 63 mM HCl, pri pH 1,2 i na 37°C, (ii) ravnotežni odnos bubrenja u deioniziranoj vodi od oko 2 ili manje i (iii) vezivanje klorida veće od 2.0 mmol po gramu polimera u SIB testu (testu simuliranog neorganskog pufera tankog crijeva ("SIB", od engl. Simulated Small Intestine Inorganic Buffer)) poslije jednog sata izlaganja polimera puferu za SIB test koji sadrži sadrži 36 mM NaCl, 20 mM NaH2PO4 i 50 mM 2-(N-morfolino)etansulfonske kiseline (MES) i podešen na pH 5,5, na 37°C.1. A pharmaceutical composition for use in the treatment of metabolic acidosis, wherein the pharmaceutical composition comprises a proton-binding cross-linked amine polymer comprising an amine residue corresponding to Formula 2b and the cross-linked amine polymer is obtained by radical polymerization of an amine corresponding to Formula 2b: [image] where m and n are independently non-negative integers; each R 12 is independently hydrogen, substituted hydrocarbyl or hydrocarbyl; R 22 and R 32 are independently hydrogen, substituted hydrocarbyl or hydrocarbyl; R42 is hydrogen, hydrocarbyl or substituted hydrocarbyl; X1 is [image] X 2 is alkyl, aminoalkyl or alkanol; each X 13 is independently hydrogen, hydroxy, alicyclic, amino, aminoalkyl, halogen, alkyl, heteroaryl, boronic acid or aryl; z is a non-negative number; and amine corresponding to Formula 2b contains at least one allyl group i the cross-linked amine polymer has (i) an equilibrium proton binding capacity of at least 5 mmol/g and a chloride ion binding capacity of at least 5 mmol/g, in an aqueous simulated gastric fluid ("SGF") buffer containing 35 mM NaCl and 63 mM HCl, at pH 1.2 and at 37°C, (ii) an equilibrium swelling ratio in deionized water of about 2 or less and (iii) chloride binding greater than 2.0 mmol per gram of polymer in the SIB test (Simulated Inorganic Small Intestine Buffer ("SIB" test ", from Eng. Simulated Small Intestine Inorganic Buffer)) after one hour of exposure of the polymer to the SIB test buffer containing 36 mM NaCl, 20 mM NaH2PO4 and 50 mM 2-(N-morpholino)ethanesulfonic acid (MES) and adjusted to pH 5.5, at 37°C. 2. Farmaceutski sastav za upotrebu prema patentnom zahtjevu 1, što umreženi aminski polimer ima vezivanje klorida koje je veće od (i) 2,5 mmol/g polimera, (ii) 3,0 mmol/g polimera, (iii) 3,5 mmol/g polimera ili (iv) 4,0 mmol/g polimera u SIB testu poslije jednog sata izlaganja polimera puferu za SIB test koji sadrži 36mM NaCl, 20 mM NaH2PO4, 50 mM 2-(N-morfolino)etansulfonske kiseline (MES) podešenog na pH 5.5 na 37 °C;2. Pharmaceutical composition for use according to claim 1, wherein the cross-linked amine polymer has a chloride binding that is greater than (i) 2.5 mmol/g polymer, (ii) 3.0 mmol/g polymer, (iii) 3.5 mmol/g polymer or (iv) 4.0 mmol/g polymer in the SIB test after one hour of exposure of the polymer to the SIB test buffer containing 36 mM NaCl, 20 mM NaH2PO4, 50 mM 2-(N-morpholino)ethanesulfonic acid (MES) adjusted to pH 5.5 at 37 °C; 3. Farmaceutski sastav za upotrebu prema patentnom zahtjevu 1 ili 2, gdje su m i z nezavisno 0-3 i n je 0 ili 1.3. Pharmaceutical composition for use according to claim 1 or 2, where m and z are independently 0-3 and n is 0 or 1. 4. Farmaceutski sastav za upotrebu prema bilo kojem od patentnih zahtjeva 1-3, gdje (i) m je pozitivan cijeli broj i R12, R22 i R42, u kombinaciji, sadrže najmanje dva alilna ili vinilna ostatka ili (ii) n je pozitivan cijeli broj i R12, R32 i R42, u kombinaciji, sadrže najmanje dva alilna ili vinilna ostatka.4. A pharmaceutical composition for use according to any one of claims 1-3, wherein (i) m is a positive integer and R12, R22 and R42, in combination, contain at least two allyl or vinyl radicals or (ii) n is a positive integer number and R12, R32 and R42, in combination, contain at least two allylic or vinyl radicals. 5. Farmaceutski sastav za upotrebu prema bilo kojem od patentnih zahtjeva 1-3, gdje je umreženi aminski polimer umrežen sa umrežavajućim agensom izabranim između: bis(3-kloropropil)amina, 1,3-dikloro-2-propanol 1,3-dikloropropana, 1-hloro-2,3-epoksipropana, tris[(2-oksiranil)metil]amina, 3-kloro-1-(3-kloropropilamino)-2-propanola, i 1,2-bis(3-kloropropilamino)etana.5. Pharmaceutical composition for use according to any one of claims 1-3, where the cross-linked amine polymer is cross-linked with a cross-linking agent selected from: bis(3-chloropropyl)amine, 1,3-dichloro-2-propanol 1,3-dichloropropane , 1-chloro-2,3-epoxypropane, tris[(2-oxiranyl)methyl]amine, 3-chloro-1-(3-chloropropylamino)-2-propanol, and 1,2-bis(3-chloropropylamino)ethane . 6. Farmaceutski sastav za upotrebu prema bilo kojem od patentnih zahtjeva 1-5, gdje je polimer sintetiziran iz amina i umrežavajućih agenasa, ili njihovih soli, izabran između: 1,4-bis(alilamino)butana, 1,2-bis(alilamino)etana, 2-(alilamino)-1-[2-(alilamino)etilamino]etana, 1,3-bis(alilamino)propana, 1,3-bis(alilamino)-2-propanola, 2-propen-1-ilamina, 1-(alilamino)-2-aminoetana, 1-[N-alil(2-aminoetil)amino]-2-aminoetana, N,N,N-trialilamina.6. Pharmaceutical composition for use according to any of claims 1-5, where the polymer is synthesized from amines and cross-linking agents, or their salts, selected from: 1,4-bis(allylamino)butane, 1,2-bis(allylamino )ethane, 2-(allylamino)-1-[2-(allylamino)ethylamino]ethane, 1,3-bis(allylamino)propane, 1,3-bis(allylamino)-2-propanol, 2-propen-1- ylamine, 1-(allylamino)-2-aminoethane, 1-[N-allyl(2-aminoethyl)amino]-2-aminoethane, N,N,N-trialylamine. 7. Farmaceutski sastav za upotrebu prema bilo kojem od patentnih zahtjeva 1-4 i 6, gdje je umreženi aminski polimer umrežen umrežavajućim agensom koji može biti korišten u reakcijama supstitucionirane polimerizacije i postpolimerizacionim reakcijama umrežavanja, gdje umrežavajući agens je jedan ili više od: dihaloalkana, haloalkiloksirana, alkiloksiran sulfonata, di(haloalkil)amina, tri(haloalkil) amina, diepoksida, triepoksida, tetraepoksida, bis (halometil)benzena, tri(halometil)benzena, tetra(halometil)benzena, i epihalohidrina.7. Pharmaceutical composition for use according to any of claims 1-4 and 6, where the cross-linked amine polymer is cross-linked with a cross-linking agent that can be used in substitution polymerization reactions and post-polymerization cross-linking reactions, where the cross-linking agent is one or more of: dihaloalkane, haloalkyloxirane, alkyloxirane sulfonate, di(haloalkyl)amine, tri(haloalkyl)amine, diepoxide, triepoxide, tetraepoxide, bis(halomethyl)benzene, tri(halomethyl)benzene, tetra(halomethyl)benzene, and epihalohydrin. 8. Farmaceutski sastav za upotrebu prema bilo kojem od patentnih zahtjeva 1-4, 6 i 7, gdje je umreženi aminski polimer umrežen umrežavajućim agensom koji može biti korišten u reakcijama supstitucionirane polimerizacije i postpolimerizacionim reakcijama umrežavanja, što je umrežavajući agens jedan ili više od: epiklorohidrin i epibromohidrin poli(epihlorohidrin), (jodometil)oksiran, glicidil tozilat, glicidil 3-nitrobenzensulfonat, 4-toziloksi-1,2-epoksibutan, bromo-1,2-epoksibutan, 1,2-dibromoetan, 1,3-dikloropropan, 1,2-dikloroetan, 1-bromo-2-kloroetan, 1,3-dibromopropan, bis(2-kloroetil)amin, tris(2-kloroetil)amin, bis(2-kloroetil)metilamin, 1,3-butadien diepoksid, 1,5-heksadien diepoksid, diglicidil etar, 1,2,7,8-diepoksioktan, 1,2,9,10-diepoksidekan, etilen glikol diglicidil etar, propilen glikol diglicidil etar, 1,4-butandiol diglicidil etar, 1,2 etandioldiglicidil etar, glicerol diglicidil etar, 1,3-diglicidil gliceril etar, N,N-diglicidilanilin, neopentil glikoldiglicidil etar, dietilen glikol diglicidil etar, 1,4-bis(glicidiloksi)benzen, rezorcinol digilcidil etar, 1,6-heksanediol diglicidil etar, trimetilolpropan diglicidil etar, 1,4-cikloheksandimetanol diglicidil etar, 1,3-bis-(2,3-epoksipropiloksi)-2-(2,3-dihidroksipropiloksi)propan, diglicidil estar 1,2-cikloheksandikarboksilne kiseline, 2,2’-bis(glicidiloksi) difenilmetan, bisfenol F diglicidil etar, 1,4-bis(2’,3’epoksipropil)perfluoro-n-butan, 2,6-di(oksiran-2-ilmeti1)-1,2,3,5,6,7-heksahidropirolo[3,4-f]izoindol-1,3,5,7-tetraon, bisfenol A diglicidil etar, etil 5-hidroksi-6,8-di(oksiran-2-ilmetil)-4-okso-4-h-kromen-2-karboksilat, bis[4-(2,3-epoksi-propiltio)fenil]-sulfid, 1,3-bis(3-glikidoksipropil) tetrametildisiloksan, 9,9-bis[4-(glicidiloksi)fenil]fluorin, triepoksiizocijanurat, glicerol triglicidil etar, N,N-diglicidil-4-glicidiloksianilin, izocijanurinska kiselina (S,S,S)-triglicidil estar, izocijanurinska kiselina (R,R,R)-triglicidil estar, triglicidil izocijanurat, trimetilolpropan triglicidil etar, glicerol propoksilat triglicidil etar, trifenilolmetan triglicidil etar, 3,7,14-tris[[3-(epoksipropoksi)propil]dimetilsililoksi]-1,3,5,7,9,11,14-heptaciklopentiltricikclo [7,3,3,15, 11]heptasiloksan, 4,4 ’metilenbis(N,N-diglicidilanilin), bis(halometil)benzen, bis(halometil)bifenil, bis(halometil)naftalen, toluen diizocijanat, akrilol klorid, metil akrilat, etilen bisakrilamid, pirometalni dianhidrid, sukcinil dihlorid, dimetilsukcinat, 3-kloro-1-(3-kloropropilamino-2-propanol, 1,2-bis(3-kloropropilamino)etan, bis(3-kloropropil)amin, 1,3-dikloro-2-propanol, 1,3-dikloropropan, 1-kloro-2,3-epoksipropan, tris[(2-oksiranil)metil]amin.8. Pharmaceutical composition for use according to any one of claims 1-4, 6 and 7, where the cross-linked amine polymer is cross-linked by a cross-linking agent that can be used in substitution polymerization reactions and post-polymerization cross-linking reactions, which cross-linking agent is one or more of: epichlorohydrin and epibromohydrin poly(epichlorohydrin), (iodomethyl)oxirane, glycidyl tosylate, glycidyl 3-nitrobenzenesulfonate, 4-tosyloxy-1,2-epoxybutane, bromo-1,2-epoxybutane, 1,2-dibromoethane, 1,3-dichloropropane , 1,2-dichloroethane, 1-bromo-2-chloroethane, 1,3-dibromopropane, bis(2-chloroethyl)amine, tris(2-chloroethyl)amine, bis(2-chloroethyl)methylamine, 1,3-butadiene diepoxide, 1,5-hexadiene diepoxide, diglycidyl ether, 1,2,7,8-diepoxyoctane, 1,2,9,10-diepoxydecane, ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, 1,4-butanediol diglycidyl ether, 1,2 ethanedioldiglycidyl ether, glycerol diglycidyl ether, 1,3-diglycidyl glyceryl ether, N,N-diglycidylaniline, neopentyl glycoldiglycidyl ether, diethylene glycol diglycidyl ether, 1,4-bis(glycidyloxy)benzene, resorcinol diglycidyl ether, 1,6-hexanediol diglycidyl ether, trimethylolpropane diglycidyl ether, 1,4-cyclohexanedimethanol diglycidyl ether, 1,3-bis-(2,3- epoxypropyloxy)-2-(2,3-dihydroxypropyloxy)propane, diglycidyl ester of 1,2-cyclohexanedicarboxylic acid, 2,2'-bis(glycidyloxy) diphenylmethane, bisphenol F diglycidyl ether, 1,4-bis(2',3' epoxypropyl)perfluoro-n-butane, 2,6-di(oxiran-2-ylmethyl)-1,2,3,5,6,7-hexahydropyrrolo[3,4-f]isoindole-1,3,5,7 -tetraone, bisphenol A diglycidyl ether, ethyl 5-hydroxy-6,8-di(oxiran-2-ylmethyl)-4-oxo-4-h-chromene-2-carboxylate, bis[4-(2,3-epoxy -propylthio)phenyl]-sulfide, 1,3-bis(3-glycidoxypropyl) tetramethyldisiloxane, 9,9-bis[4-(glycidyloxy)phenyl]fluorine, triepoxyisocyanurate, glycerol triglycidyl ether, N,N-diglycidyl-4-glycidyloxyaniline , isocyanuric acid (S,S,S)-triglycidyl ester, isocyanuric acid (R,R,R)-triglycidyl ester, triglycidyl isocyanurate, trimethylolpropane triglycidyl ether, glycerol propoxylate triglycidyl ether, triphenylolmethane triglycidyl ether, 3,7,14-tris[[3-(epoxypropoxy)propyl]dimethylsilyloxy]-1,3,5,7,9,11,14-heptacyclopentyltricyclo [7,3, 3,15, 11]heptasiloxane, 4,4'methylenebis(N,N-diglycidylaniline), bis(halomethyl)benzene, bis(halomethyl)biphenyl, bis(halomethyl)naphthalene, toluene diisocyanate, acrylol chloride, methyl acrylate, ethylene bisacrylamide , pyrometallic dianhydride, succinyl dichloride, dimethylsuccinate, 3-chloro-1-(3-chloropropylamino-2-propanol, 1,2-bis(3-chloropropylamino)ethane, bis(3-chloropropyl)amine, 1,3-dichloro- 2-propanol, 1,3-dichloropropane, 1-chloro-2,3-epoxypropane, tris[(2-oxiranyl)methyl]amine. 9. Farmaceutski sastav za upotrebu prema bilo kojem prethodnom patentnom zahtjevu, gdje je umreženi aminski polimer pripremljen umrežavanjem intermedijera koji sadrži amin sa polifunkcionalnim umrežavajućim agensom.9. A pharmaceutical composition for use according to any preceding claim, wherein the cross-linked amine polymer is prepared by cross-linking an amine-containing intermediate with a polyfunctional cross-linking agent. 10. Farmaceutski sastav za upotrebu prema bilo kojem prethodnom patentnom zahtjevu, gdje umrežavajući aminski polimer ima ravnotežni odnos bubrenja u deioniziranoj vodi od: (i) 1,5 ili manji, ili (ii) 1 ili manji.10. A pharmaceutical composition for use according to any preceding claim, wherein the crosslinking amine polymer has an equilibrium swelling ratio in deionized water of: (i) 1.5 or less, or (ii) 1 or less. 11. Farmaceutski sastav za upotrebu prema bilo kojem prethodnom patentnom zahtjevu, gdje umrežavajući aminski polimer ima molarni odnos vezivanja kloridnog iona prema fosfatnom ionu od: (i) bar 0,5:1, (ii) bar 1:1, ili (iii) bar 2:1; tim redom, u vodenom simuliranom neorganskom puferu tankog crijeva ("SIB") koji sadrži 36 mM NaCl, 20 mM NaH2PO4 i 50 mM 2-(N-morfolino)etansulfonske kiseline (MES) i podešen je do pH 5,5, na 37°C.11. A pharmaceutical composition for use according to any preceding claim, wherein the crosslinking amine polymer has a chloride ion to phosphate ion binding molar ratio of: (i) at least 0.5:1, (ii) at least 1:1, or (iii) at least 2:1; respectively, in aqueous simulated small intestine inorganic buffer ("SIB") containing 36 mM NaCl, 20 mM NaH2PO4, and 50 mM 2-(N-morpholino)ethanesulfonic acid (MES) and adjusted to pH 5.5, at 37 °C. 12. Farmaceutski sastav za upotrebu prema bilo kojem prethodnom patentnom zahtjevu, gdje umreženi aminski polimer ima kapacitet vezivanja protona od najmanje 10 mmol/g i kapacitet vezivanja kloridnih iona od najmanje 10 mmol/g, u vodenom puferu simulirane želudačne tekućine ("SGF") koji sadrži 35 mM NaCl i 63 mM HCl, pri pH 1,2 i na 37°C.12. A pharmaceutical composition for use according to any preceding claim, wherein the cross-linked amine polymer has a proton binding capacity of at least 10 mmol/g and a chloride ion binding capacity of at least 10 mmol/g, in an aqueous simulated gastric fluid ("SGF") buffer which contains 35 mM NaCl and 63 mM HCl, at pH 1.2 and at 37°C. 13. Farmaceutski sastav za upotrebu prema bilo kojem prethodnom patentnom zahtjevu, gdje u spomenutom postupku: (i) manje od 1 g natrija ili kalija je davano dnevno; (ii) manje od 0,5 g natrija ili kalija je davano dnevno (iii) manje od 0,1 g natrija ili kalija je davano dnevno ili (iv) nije davan natrij ili kalij.13. Pharmaceutical composition for use according to any previous patent claim, where in the mentioned process: (i) less than 1 g of sodium or potassium was administered per day; (ii) less than 0.5 g of sodium or potassium was administered per day (iii) less than 0.1 g of sodium or potassium was administered per day or (iv) no sodium or potassium was given. 14. Farmaceutski sastav za upotrebu prema bilo kojem prethodnom patentnom zahtjevu, gdje u spomenutom postupku je davana dnevna doza manja od: (i) 20g, (ii) 15g, (iii) 10g, (iv) 5g, (v) 4g, ili (vi) 3g.14. Pharmaceutical composition for use according to any previous patent claim, where in the mentioned procedure a daily dose of less than: (i) 20 years, (ii) 15 years, (iii) 10 years, (iv) 5 years, (v) 4g, or (vi) 3 years. 15. Farmaceutski sastav za upotrebu prema bilo kojem prethodnom patentnom zahtjevu, gdje je dnevna doza davanja: (i) jednom dnevno, (ii) dva puta dnevno, ili (iii) tri puta dnevno.15. A pharmaceutical composition for use according to any preceding patent claim, wherein the daily administration dose is: (i) once a day, (ii) twice a day, or (iii) three times a day. 16. Farmaceutski sastav za upotrebu prema bilo kojem prethodnom patentnom zahtjevu, gdje u spomenutom postupku dnevna doza dovodi do održavanog porasta bikarbonata u serumu: (i) ≥1,6 mEq/L, (ii) ≥2 mEq/L, (iii) ≥3 mEq/L, (iv) ≥5 mEq/L, ili (v) ≥10 mEq/L,16. Pharmaceutical composition for use according to any previous patent claim, where in the mentioned procedure the daily dose leads to a sustained increase in bicarbonate in the serum: (i) ≥1.6 mEq/L, (ii) ≥2 mEq/L, (iii) ≥3 mEq/L, (iv) ≥5 mEq/L, or (v) ≥10 mEq/L, 17. Farmaceutski sastav za upotrebu prema bilo kojem prethodnom patentnom zahtjevu, gdje je u spomenutom postupku doza podešavanja na osnovu vrijednosti bikarbonata u serumu pacijenta kojem je potrebno liječenje ili drugih indikatora acidoze.17. A pharmaceutical composition for use according to any preceding patent claim, wherein in said procedure the dose is adjusted based on the bicarbonate value in the serum of the patient in need of treatment or other indicators of acidosis. 18. Farmaceutski sastav za upotrebu prema bilo kojem prethodnom patentnom zahtjevu, gdje je metabolička acidoza naznačena time što je vrijednost bikarbonata u serumu manja od 22 mEq/l.18. A pharmaceutical composition for use according to any preceding claim, wherein metabolic acidosis is indicated by a serum bicarbonate value of less than 22 mEq/l.
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